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Watch 58 minutes of gender bending humiliation as Mistress Autumn teases and transforms slave manhole. The tall submissive is sissified and turned into a tongue slave beneath Mistress Autumn's hot pussy. His nipples are treated to some intense torment as he licks beneath Her. She penetrates his asspussy with Her dildo and he worships Her feet before being violated at the end of Her strap-on.

Mistress Autumn is interviewing Her next session. Slave manhole has quite the urge to be feminized She discovers. He is ordered to stand and strip down for Her and She checks out his pathetic clit. She uses Her feet on him and he gets erect. Mistress Autumn slaps him soft and then plays with Herself to tease him. She orders him into the transformation room to begin his journey to womanhood. Laying naked beneath Her feet he suffers verbal humiliation and swallows Her spit.

Mistress Autumn stands tall in bra and panties over Her naked submissive. She stomps on his useless cock and balls to keep him in check and then orders him to fetch a pair of pantyhose from the foot locker. He puts these on under Her watchful eye and then has his ass inspected as She tells him She will be penetrating his tiny asspussy with Her dildos. Mistress Autumn has him put on a dress and high heels of Her choosing and then puts a blonde wig on him. She tells him he has no real tits and teasingly removes Her bra and tells him to worship Hers. She moves to get Her strap-on and has him suck it like a 'three dollar whore.

Her sissy standing in his dress and heels is wrapped tight in bondage tape and tied in pantyhose by Mistress Autumn. She orders him to his back and decides to show him what a real woman tastes like. His tongue is directed to Her clit and he is used for oral service for quite some time. Mistress Autumn turns and sits Her pussy down on his face. She applies the Tower of Pain nipple clamps and turns the screw until his nipples are stretched. She gets quite a reaction using the razor sharp pinwheel on his nipples and enjoys the groans as he licks Her pussy.

Mistress Autumn remains perched on the face of Her submissive. He is in some pain from the nipple torment and She screws the clamps up until they are pulled off his nipples, eliciting a load scream. She rewards his tongue service by allowing him foot worship and then rolls him over to insert a dildo into his asspussy. She massages the dildo in with Her feet and then turns him to play footsie with his cock. She moves the table and puts on Her strap-on as he waits in anticipation.

Mistress Autumn sits on the bench wearing Her strap-on and orders Her humiliated, cross-dressed submissive to back himself into Her cock. He groans as he is violated and then is made to fuck Her slow and then fast. She tells him to play with his little clitty as he performs at the end of Her cock. She pulls Her cock out of him and sends him to the middle of the room. Mistress Autumn then fucks him soundly from behind. She spanks him with Her high heel and verbally humiliates him.

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